


and they were roommates

by hellhoundsprey



Series: winkline bingo 2021 [1]
Category: Supernatural
Genre: Alternate Universe - College/University, Alternate Universe - No Powers, Alternate Universe - Normal Life, M/M, Plot What Plot/Porn Without Plot, Sex Toys, error 404: no stereotypical top/bottom dynamics found
Language: English
Status: Completed
Published: 2020-11-25
Updated: 2020-11-25
Packaged: 2021-03-09 22:13:35
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,409
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/27713221
Author URL: https://archiveofourown.org/users/hellhoundsprey/pseuds/hellhoundsprey
Summary: Oh my god they wereroommates.winkline bingo 2021: 09 college AU
Relationships: Jack Kline/Sam Winchester
Series: winkline bingo 2021 [1]
Series URL: https://archiveofourown.org/series/2026918
Comments: 8
Kudos: 36





	and they were roommates

**Author's Note:**

> Comfort shipping to heal all emotional wounds? Yes.
> 
> Sam and Jack are the same age in this one.

“D-does it—hurt?”

Sam shakes his head and smiles. “Nah. Here. See?”

Jack looks, and he sees. Swallows, and Sam kisses him again, like Jack would need any distraction.

Sam murmurs, “Feels so fucking good,” and Jack is the one nodding, now. Sam’s thighs twitch further open as Jack wraps his hand around Sam’s cock, strokes him slow and easy, just like he does with his own. Drawing it out—even if just a little.

Jack’s stayed through Sam’s brother visiting, but when it’s just him and Sam, it’s—different.

The ancient mattress springs sing off-tune for Sam’s arm picking up speed. Sam’s choked-off, “Fuck…” How he bites his lower lip with his eyes closed, lost, focused.

Even halfway through this semester, Jack is still entirely mesmerized. He licks his lip in sympathy. “Are you going to come?”

“Don’t stop,” and Jack would never.

He sits back far enough to look between them—where he is working them both and lower, where Sam fucks himself with one of his toys. It’s huge and the shape is odd (yet unmistakable) and Sam’s body clings to it despite the healthy amount of lube. Jack’s nuts tense at the sight.

He switches to a one-handed grip so he can balance his weight on his other arm, can spread his knees wider and slide their dicks against each other. It sends Sam’s breath hitching and Sam reaches his free hand up to grab Jack’s hair, yank him down for kisses, and Jack knows his friend’s tells by now.

Sam comes quiet and intense. Like a storm, always, taking Jack with him. The sweat between them soaks into Jack’s rucked-up but slowly slipping down tee and he sighs, shivering. Sam’s body has fully melted into the bed at this point. He doesn’t interfere with Jack burying his face in the nape of his neck.

Ragged, “Fuck,” and Jack just hums in approval. Their stuffy tiny room. The borrowed and/or inherited furniture from former frat brothers. Cheap body wash.

Sam’s one-armed hug turns into him shifting his arm lower, until he can reach Jack’s ass. Can push his long fingers right into the cleft of it and Jack hums, blindly, and flinches.

“Hm…”

“Yeah?”

“Too soon,” but Sam kiss-sucks at his neck, tucks his fingers—in, thanks to come and traces of lube. Not much warning. Jack’s hips cringe inwards on instinct. He tilts them back out with a huff and pushes himself up on his elbow.

Sam nurses at his mouth immediately. Languid and sweet and when he finally opens his eyes, they’re so dark Jack can’t even see a hint of one of their colors.

He smiles as he informs, “Sucking them right up,” and Jack flushes further, and he mumbles something unimportant that gets drowned out by Sam, licking into his mouth. “So hungry,” and Jack’s never been like this with anyone, never thought he’d—want to.

Sam is the exception to everything.

Jack’s spent cock thrums tight with Sam rubbing him out from the inside. His nuts are still tight, the orgasm still lingering.

He groans.

“Like that?” and Sam reaches his other hand down as well, and Jack nods and tells him, “Yes,” and Sam kisses his ear, holds his ass open and fucks his fingers in with the other hand.

“You wanna try one?”

“S-Sam—!”

Sam laughs. “No?”

Jack makes a face.

Sam kisses him on the cheek. “There’s a small one. I think.”

“You _think_?”

“Uh, size is pretty relative.” Another quick kiss. “Want me to get it?”

Jack uh-huhs and Sam’s smile brightens in the darkness of the room. He produces something from inside his nearby nightstand and helps Jack turn around, lays him out on his back before he lifts his legs for him, bends him in the middle until Jack can feel his blood getting trapped in his head.

Sam soothes, “Here,” and drags his tongue over Jack’s asshole, once, and Jack flinches for it, and it’s all too much.

He can’t mind. Not now.

Not with Sam smiling like mischief as he flops the already condom-wrapped toy down over Jack’s taint, and Jack gasps and tries to scoot into a more comfortable position to see better, more, all of it.

A…tentacle.

Slim, yeah, but…

“It’s— _long_ …”

“Don’t have to go deep,” offers Sam.

Jack blinks for the cold rush of lube, and on the next inhale he takes, the toy pushes into him.

Easy. Foreign.

His head is running so so hot.

Jack hears, “You like it?” and doesn’t have words. Just—watches it, inch after inch disappearing inside of him, how its circumference increases gradually until it’s as wide as those two of Sam’s fingers and _more_ , and.

Sam chuckles.

He dips his head down easily to lap up Jack’s taint. Kisses his sac, once and cute, and rocks the toy in-out for the first time.

Jack’s cock stirs—irritated, interested. Reeling.

“Oh,” he says, and Sam does it again. And again.

“Good? Yeah?” and Jack thinks he nods, yes, yeah. “Can I kiss you, baby? Want me to kiss you?”

Jack nods for that, too, naturally.

Sam does what he said he’d do. Lowers Jack into his lap so he can reach, and it’s then that Jack realizes he’s rocking himself on the toy, still, and, yeah, recovery time is officially over.

Slurred, “You’re so hot,” against Jack’s mouth, and Jack can only—whimper. Lets his legs fall as open as they will go so Sam has room to move, so Sam can fuck him easy.

The toy _is_ deep, now, he thinks, considering how wide it spreads him on each push-in. The many suckers on the tentacle drag like crazy on every quick, playful stroke.

Jack hears, “Maybe we’ll try my cock next, huh?” and he seizes with his too-fast orgasm, and he buries his nails in Sam’s back and holds on, shakes through it and rocks back on the toy still working him.

Sweet, “Baby,” and Jack sobs, embarrassed, and turns his face to hide—useless, of course, since this isn’t the first time this happened (to either of them). He feels Sam kissing his cheek, his temple, his ear. Hot breath, drag of lips, of barely-there stubble. “Does it turn you on, yeah? Imagining this is me?”

Jack utters his airless, “Yes,” with the next emphasized push of the tentacle. He curls his arms tighter around Sam, Sam’s shoulders, and he kisses him anew. Always, always. Never enough, not when they are like this. Just them.

Sam lets their mouths part with a wet pop. “Let me keep fucking you with this while you suck me off?”

They struggle into position, and being face to face with another guy’s raging boner is about as shame-inducing as having said guy groaning underneath you and tugging your balls aside to see better.

Dreamy, “Fuck,” and Jack sinks his mouth down where it’s needed.

Sam can purr like a cat for this.

Lower, “Fuck, _fuck_ ,” when Jack manages to flirt his hand down, finds the base of the toy to help rocking it into Sam’s ass. Sam’s breath comes heavy and hot against the back of Jack’s thigh, and Jack’s head is spinning.

He still can’t make sense of why—him.

“So close,” and not much longer, then.

Sam whimpers for Jack switching his hand from the toy to the inches of cock his mouth can’t reach, to work the last drops out. Without external resistance, the toy slips from Sam’s clenched ass, wet and huge and Jack splutters, helps threading it back in only to get another weak tremble out of Sam’s cock.

“Fuck…”

Jack pushes himself up and around until he can find a nearby glass from the nightstand to spit into. When he meets Sam’s eyes again, his classmate is watching him, smiling.

“What?”

“Nothing.” Sam pats his chest. “Come here.”

They get rid of the toys (tiled floors thanks to the aftermath of Beerfest 2017) and Sam lets him cuddle up while he is still busy wiping down himself first and Jack later. The tissues land with the toys, noiselessly. Carelessly.

With Jack’s chin propped up on the back of his hand, he is free to watch Sam settling in—wiping his own face, flicking his bangs out of his eyes. He catches him watching and prompts, “What?” and drapes one arm around Jack, folds the other underneath his own head.

Jack says, honestly, smiling, “Nothing.”

**Author's Note:**

> I've thrown together a little winkline bingo card for myself just for funsies. I'll go through it square by delicious square. Slapped a 2021 on there for good measure since I doubt I'll get much done during Christmas sale season, but...it's a happy place, so I'm keeping it on the side.


End file.
